Talking to Strangers: Chicago, IL

Hooksexup asks deeply personal questions to people we've just met — this week, at SlutWalk Chicago.

By Ruth Tam

Ashley, 26

What do you do?
I'm a writer and a musician.

Do you get a lot of dates?
Not as many as I would hope. I'm a sax player, and I'll play in bands and stuff, and it seems that guys I play with always get a lot of girls, but it might be intimidating to see a girl up there.

Where are you from originally?
Northern California.

How do you think the dating scene here compares?
In school, it was a lot easier, because you're around the same people all the time. In the city, you're around people so much, but you talk to so few of them. I feel like I'm almost more alone in a giant city than I am in a small town.

So do you regret moving?
No, I love Chicago.

What do you look for?
Intelligence, humor, and looks. I'm an atheist and it's important for me to be with someone who has similar spiritual beliefs, or lack thereof.

So when you see a smart, good-looking, funny atheist, how do you go about impressing them?
I just start talking about stuff I've read and try to be funny. I wait 'til they come to me. Actually, I get really nervous. I just like, shut down.

Do you have any funny hookup stories?
One time, I was hooking up with this guy and we were both really drunk, and he went down on me, and I came, and he just, like, kept going. There was just this moment where I was like, uh, do I be polite? What's the thing to do here? And so I said, "Uh, you know I came, right?" and he was just like, "Oh, okay." Of course, I knew all his friends, and so the next day, I'm talking to one of our mutual friends, and he goes, "Uh, you know I came, right?"

Do you have any crazy exes?
Going on with the atheism thing, I'm really into critical thinking. I don't believe anything unless there's good scientific evidence for it. So, I had just started dating this guy, and it was going fine, but every so often he would say things like, "Well, obviously there are aliens on earth." And I thought he was joking, but finally it all came to a head one day when he said 9/11 was actually an inside job. He had talked about UFOs before, but he came out and said, "Yeah, 9/11 was obviously the government attacking its citizens." And I was like, "No." He proceeded to play me all these podcasts and videos he had seen and I just had to get out of there. The problem was, he was gorgeous.

Has anyone ever offended you in the bedroom?
There was one guy who as soon as he was done going down on me, he would get up, run to the bathroom and wash his mouth out with Listerine.

What do you wish you could change about the opposite sex?
The opposite sex believes that women need to be coddled and cared for. I prefer a guy who treats me like a friend.

So are you looking for a fuck buddy?
A fuck buddy in a manner of speaking, but still someone who's also my boyfriend. Emotion and love is important, but I don't want to be treated like some sort of doll.

 

Doug, 28

What do you do?
I work for an online university. I'm an academic advisor.

Where are you from?
Seattle.

How does dating life in Seattle compare?
Seattle guys are weird. I've never met a guy from Seattle who hasn't ended up a total weirdo and kind of a jerk in the end. They're really laid back, but they don't give a shit about you. I love Seattle, but the people can be a little cold.

How many times have you been in love?
Three.

Do you have any crazy exes?
The first guy I told I was in love with him. After we had our moment of "I love you," he literally turned around and said, "Okay, I'm gonna act weird around you now," and wouldn't talk to me after that.

Do you think it's better that he acknowledged he was being weird, or was it just horrible?
It was just horrible. Because I was expecting this whole "I love him, he loves me too, and everything will be beautiful!" And that's not what happened.

What did you learn from that?
Don't date guys who are not okay with being gay. Because they're psycho.

Before you met your boyfriend, where would you find guys?
I went online to find dates. I was into meeting them online and then getting to know them in person right away. I prefer to meet people online because if I went to the bars, I wouldn't be able to hear anything, so I wouldn't remember your name.

Do you think people hide their true selves online?
Yes and no. I think people hide their true selves online, but a lot of people do it in really obvious ways, like posting a fake picture of themselves. But people hide themselves in real life, too. You just take your chances.

Any funny or embarrassing hookup stories?
When I was still in Seattle, there was a guy who invited me to come hang out with him and his roommate. So I show up, thinking we're friends, and when I get there, he says, "Oh, my roommate's gone," and that was warning number one. And he said he had to go take a shower and get ready for an evening out. When he came back, he was wearing just a towel, and he turned around, looked at me, dropped the towel, and said, "Do you think I should trim my pubes?" That wasn't very attractive.

So he was coming on to you?
Yeah, he was coming on to me with that line, and it did not work. His pubes were already very clearly trimmed and groomed well, so I was like, "No, I think they're fine." Then I asked to be taken home.

So is that the furthest anyone's gone?
Yes. The most overtly desperate.

What do you look for?
I was closeted and in denial for so long that I wasn't conscious of what my type was. I always fell for the guys who seemed shy and misunderstood. Sometimes it works out and those guys can be really nice, and sometimes they turn out to be total weirdos.

 

Matt, 26

What do you do?
I'm a FedEx delivery driver.

Do you get a lot of dates with your job?
There's a lot of flirting, but since they're customers, I don't take it further.

There's that delivery-man fantasy, though.
Yeah, it's not as luxurious as the porn industry makes it out to be.

What's the craziest place you've had sex?
Well, I lost my virginity to an older woman. She was a twenty-seven-year-old mom. I was twenty. Her son was watching The Polar Express in her bedroom and she kicked him out and we banged.

So, she rode the Polar Express?
Yes.

How did you meet?
I was going to college and she was a student too. We met at the student lounge.

What do you look for in a girl?
I'm kind of emotionally bankrupt. I kind of look for relationships that won't work out. I'm afraid of commitment. I honestly go for cougars because I know it won't progress to anything serious.

Is there a place you go to pick up older women?
Just regular bars. Some older women like older karaoke.

Oh, is karaoke your move? Do you have a special song?
I do a Ben Folds Five song, "Song for the Dumped." It goes like [singing] "Well, fuck you, too. Give me my money back, bitch!" So you get 'em laughing and then they ask if someone dumped you and you can play up their sympathy.

Any embarrassing stories?
I got appendicitis. I was bedridden for two days straight, and this cute nurse comes in and she's talking to me, asking me about what I want to do after high school. I thought she was into me; I didn't realize that after two days in a hospital, you look like absolute shit. I don't care who you are, you could be Tyra Banks and... anyway. So, we're talking, and I think, "Maybe when I get out of here, I can get her number." I come to find out that the reason she was trying to earn my trust was that she needed to prep me for surgery. She comes in one day and says, "The doctor wants you to be cleaned." And I'm like, "All right! Sponge bath! This is kinda nice!" And she's like, "I need to give you an enema." So the whole point of chatting me up was so she could inject cold water up my rectal cavity.

So did you ask for her number?
No. But it doesn't end there. An appendectomy is the gift that keeps on giving. Afterwards, I had to go in for a physical, and it was done by this old German lady. I had this type of surgery called a scope, and it doesn't leave scars. I had just done some manscaping. And she's doing the "coughing," where doctors grab your crotch and tell you to cough and she cups my crotch and says, "This is very elegant." I thought she meant my manscaping was elegant and I'm like, "Thank you! I try to keep trim." But it turns out she was talking about my appendectomy procedure. She was admiring the lack of scars.

Any dating dealbreakers?
I don't know. I have pretty low standards. I guess if she's overly religious. I left religion myself, so if someone tried to pull me back in, it's irreconcilable. Oh, once, I took a cougar to a Vietnamese restaurant and she was telling me this story about how she didn't like Purdue because there were "too many Asian people." She was hot, but clearly very stuck up. She tried to get with me later at her place and what she said was still stuck in my head and I just got up and left. That probably the coldest way to break up with someone. But, like I said… I'm emotionally bankrupt.

What would you change about the opposite sex?
I wish they were more aggressive sexually. I think that's why I like cougars. I can be a little shy at times. Even though I told you about shaving my pubes and shit. I'm a weird kind of outgoing and that turns off people.